Ethyl 3,4-dimethyl-1H-pyrrole-2-carboxyl-ate.

The non-H atoms of the title compound, C(9)H(13)NO(2), are almost coplanar (r.m.s. deviation = 0.0358 Å). Weak inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along the b axis with graph-set motif C(5). The chains are further linked into a three-dimensional network by C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

Schiff bases containing pyrrole units have been extensively investigated due to their excellent coordination abilities, see: Wu et al. (2003 ▶). For our studies on bis­(pyrrol-2-yl-methyl­ene­amine) ligands, see: Wang et al., (2008 ▶). For a similar structure, 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxyl­ate, see Wu et al. (2009 ▶). For the preparation, see: Helms et al. (1992 ▶). For graph-set motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C9H13NO2

M = 167.20

Monoclinic,

a = 7.7485 (2) Å

b = 7.0611 (2) Å

c = 17.2167 (5) Å

β = 95.103 (2)°

V = 938.24 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.28 × 0.26 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.977, T max = 0.985

8174 measured reflections

2146 independent reflections

1579 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.136

S = 1.04

2146 reflections

112 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003179X/fb2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003179X/fb2205Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H13NO2	F(000) = 360
Mr = 167.20	Dx = 1.184 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3131 reflections
a = 7.7485 (2) Å	θ = 2.4–24.8°
b = 7.0611 (2) Å	µ = 0.08 mm−1
c = 17.2167 (5) Å	T = 296 K
β = 95.103 (2)°	Block, colourless
V = 938.24 (5) Å3	0.28 × 0.26 × 0.18 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2146 independent reflections
Radiation source: fine-focus sealed tube	1579 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→10
Tmin = 0.977, Tmax = 0.985	k = −9→9
8174 measured reflections	l = −22→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.1432P] where P = (Fo2 + 2Fc2)/3
2146 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 e Å−3
49 constraints

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O2	0.14704 (13)	0.48430 (14)	0.11453 (6)	0.0534 (3)
O1	−0.00527 (14)	0.33077 (15)	0.19987 (7)	0.0615 (3)
N1	0.24389 (16)	0.04205 (17)	0.20998 (7)	0.0498 (3)
H1	0.1597	0.0168	0.2377	0.060*
C2	0.41028 (18)	0.1886 (2)	0.12961 (8)	0.0463 (4)
C7	0.12075 (18)	0.34064 (19)	0.16247 (8)	0.0445 (3)
C1	0.25621 (17)	0.20054 (19)	0.16438 (8)	0.0422 (3)
C8	0.0178 (2)	0.6323 (2)	0.10833 (10)	0.0582 (4)
H8A	0.0125	0.6946	0.1583	0.070*
H8B	−0.0953	0.5796	0.0923	0.070*
C4	0.3843 (2)	−0.0672 (2)	0.20438 (10)	0.0561 (4)
H4	0.4060	−0.1820	0.2299	0.067*
C3	0.49035 (19)	0.0178 (2)	0.15508 (9)	0.0521 (4)
C9	0.0697 (3)	0.7705 (3)	0.04886 (11)	0.0686 (5)
H9A	0.1837	0.8179	0.0644	0.103*
H9B	−0.0111	0.8738	0.0447	0.103*
H9C	0.0699	0.7085	−0.0007	0.103*
C5	0.4845 (2)	0.3287 (3)	0.07667 (11)	0.0702 (5)
H5A	0.3973	0.3650	0.0363	0.105*
H5B	0.5806	0.2725	0.0536	0.105*
H5C	0.5234	0.4386	0.1060	0.105*
C6	0.6620 (2)	−0.0563 (3)	0.13353 (13)	0.0784 (6)
H6A	0.7528	0.0278	0.1533	0.118*
H6B	0.6604	−0.0640	0.0778	0.118*
H6C	0.6820	−0.1799	0.1557	0.118*

	U11	U22	U33	U12	U13	U23
O2	0.0535 (6)	0.0449 (6)	0.0639 (7)	0.0109 (4)	0.0178 (5)	0.0096 (5)
O1	0.0585 (7)	0.0564 (7)	0.0742 (8)	0.0072 (5)	0.0314 (6)	0.0035 (5)
N1	0.0523 (7)	0.0466 (7)	0.0523 (7)	0.0007 (5)	0.0151 (6)	0.0061 (5)
C2	0.0450 (7)	0.0479 (8)	0.0469 (8)	0.0013 (6)	0.0092 (6)	0.0019 (6)
C7	0.0464 (7)	0.0416 (7)	0.0467 (8)	−0.0002 (6)	0.0107 (6)	−0.0038 (6)
C1	0.0433 (7)	0.0403 (7)	0.0440 (7)	0.0001 (5)	0.0091 (6)	0.0021 (6)
C8	0.0595 (9)	0.0451 (8)	0.0711 (10)	0.0133 (7)	0.0119 (8)	0.0018 (8)
C4	0.0615 (9)	0.0468 (8)	0.0595 (9)	0.0088 (7)	0.0025 (7)	0.0079 (7)
C3	0.0462 (8)	0.0545 (9)	0.0560 (9)	0.0084 (6)	0.0059 (7)	−0.0004 (7)
C9	0.0832 (12)	0.0541 (10)	0.0685 (11)	0.0128 (9)	0.0066 (9)	0.0102 (9)
C5	0.0643 (10)	0.0732 (12)	0.0775 (12)	0.0024 (9)	0.0302 (9)	0.0191 (9)
C6	0.0571 (10)	0.0842 (13)	0.0950 (14)	0.0260 (9)	0.0134 (10)	0.0026 (11)

O2—C7	1.3347 (17)	C4—C3	1.371 (2)
O2—C8	1.4446 (17)	C4—H4	0.9300
O1—C7	1.2186 (17)	C3—C6	1.506 (2)
N1—C4	1.3440 (19)	C9—H9A	0.9600
N1—C1	1.3752 (17)	C9—H9B	0.9600
N1—H1	0.8600	C9—H9C	0.9600
C2—C1	1.3849 (19)	C5—H5A	0.9600
C2—C3	1.409 (2)	C5—H5B	0.9600
C2—C5	1.494 (2)	C5—H5C	0.9600
C7—C1	1.4406 (19)	C6—H6A	0.9600
C8—C9	1.495 (2)	C6—H6B	0.9600
C8—H8A	0.9700	C6—H6C	0.9600
C8—H8B	0.9700
C7—O2—C8	116.91 (12)	C4—C3—C2	107.21 (13)
C4—N1—C1	109.16 (12)	C4—C3—C6	126.27 (15)
C4—N1—H1	125.4	C2—C3—C6	126.51 (15)
C1—N1—H1	125.4	C8—C9—H9A	109.5
C1—C2—C3	106.86 (12)	C8—C9—H9B	109.5
C1—C2—C5	128.10 (13)	H9A—C9—H9B	109.5
C3—C2—C5	125.02 (13)	C8—C9—H9C	109.5
O1—C7—O2	122.94 (13)	H9A—C9—H9C	109.5
O1—C7—C1	124.41 (14)	H9B—C9—H9C	109.5
O2—C7—C1	112.65 (12)	C2—C5—H5A	109.5
N1—C1—C2	107.69 (12)	C2—C5—H5B	109.5
N1—C1—C7	118.98 (12)	H5A—C5—H5B	109.5
C2—C1—C7	133.32 (13)	C2—C5—H5C	109.5
O2—C8—C9	107.22 (13)	H5A—C5—H5C	109.5
O2—C8—H8A	110.3	H5B—C5—H5C	109.5
C9—C8—H8A	110.3	C3—C6—H6A	109.5
O2—C8—H8B	110.3	C3—C6—H6B	109.5
C9—C8—H8B	110.3	H6A—C6—H6B	109.5
H8A—C8—H8B	108.5	C3—C6—H6C	109.5
N1—C4—C3	109.09 (14)	H6A—C6—H6C	109.5
N1—C4—H4	125.5	H6B—C6—H6C	109.5
C3—C4—H4	125.5
C8—O2—C7—O1	0.1 (2)	O1—C7—C1—C2	−177.02 (15)
C8—O2—C7—C1	179.83 (13)	O2—C7—C1—C2	3.3 (2)
C4—N1—C1—C2	−0.19 (16)	C7—O2—C8—C9	−177.04 (13)
C4—N1—C1—C7	−178.84 (13)	C1—N1—C4—C3	−0.06 (18)
C3—C2—C1—N1	0.37 (16)	N1—C4—C3—C2	0.29 (18)
C5—C2—C1—N1	−178.16 (16)	N1—C4—C3—C6	179.24 (16)
C3—C2—C1—C7	178.74 (16)	C1—C2—C3—C4	−0.40 (17)
C5—C2—C1—C7	0.2 (3)	C5—C2—C3—C4	178.18 (16)
O1—C7—C1—N1	1.2 (2)	C1—C2—C3—C6	−179.35 (16)
O2—C7—C1—N1	−178.46 (12)	C5—C2—C3—C6	−0.8 (3)

Cg1 is the centroid of the N1,C1–C4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.13	2.9264 (16)	154.
C5—H5A···O2	0.96	2.60	2.962 (2)	103.
C4—H4···Cg1ii	0.93	2.92	3.7520 (17)	149
C9—H9A···Cg1iii	0.96	2.86	3.650 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.13	2.9264 (16)	154
C4—H4⋯Cg1ii	0.93	2.92	3.7520 (17)	149
C9—H9A⋯Cg1iii	0.96	2.86	3.650 (2)	141

Symmetry codes: (i) ; (ii) ; (iii) .